HCID 14209951, compound → HCID 14209957, compound

HRID 1196885Notes

Reaction equation

HRID 1196885 reaction equation
[C:1]([NH:9][C:10]1[CH:11]=[C:12]2[C:17](=[CH:18][C:19]=1[N+:20]([O-])=O)[NH:16][C:15](=[O:23])[CH2:14][CH2:13]2)(=O)[C:2]1[CH:7]=[CH:6][N:5]=[CH:4][CH:3]=1>[Pd].CO>[N:5]1[CH:6]=[CH:7][C:2]([C:1]2[NH:9][C:10]3=[CH:11][C:12]4[CH2:13][CH2:14][C:15](=[O:23])[NH:16][C:17]=4[CH:18]=[C:19]3[N:20]=2)=[CH:3][CH:4]=1

Participants

4

Reactant 1

HCID 14209951HCID 14209951, compound

Product 1

HCID 14209957HCID 14209957, compound

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

2.4 g. (7.7 mmole) 6-isonicotinoylamino-7-nitro-1,2,3,4-tetrahydroquinolin-2-one were hydrogenated in 100 ml. methanol in the presence of 0.4 g. 10% palladium on charcoal. After filtering off the catalyst and evaporating the filtrate, the residue was boiled for 24 hours with 80 ml. ethanol and 15 ml. concentrated hydrochloric acid. The evaporation residue was treated with water and ammonia, filtered off with suction and recrystallized from methanol to give 1.3 g. (62% of theory) of the title compound; m.p. above 300° C.

Workup

  1. filtrationAfter filtering off the catalyst
  2. customevaporating the filtrate
  3. additionThe evaporation residue was treated with water and ammonia
  4. filtrationfiltered off with suction
  5. customrecrystallized from methanol
  6. customto give 1.3 g

Sources & evidence

ORD record
ord-2644af101bf8488db91ee83776dbea89
Source dataset
uspto-grants-1992_05
Patent number
US05116843

Reaction notes

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